25263-44-9

2-(3-Hydroxyphenyl)acetonitrile is used in preparation of Pyrrolidine Sulfonamide compounds as TRPV4 antagonists.

Step 1: Dissolve 2-(3-methoxyphenyl)acetonitrile (2 g, 13.59 mmol) in 13 mL of anhydrous dichloromethane under nitrogen protection and cool to 0°C. A 1 M solution of boron tribromide in dichloromethane (28.54 mL, 28.54 mmol) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the mixture was poured into ice water and extracted three times with dichloromethane. The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate (80/20) as eluent to give 1.28 g (71% yield) of 2-(3-hydroxyphenyl)acetonitrile.

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